Ammonia → 5-Phenylsulphonyl-6-methyl-1,3-benzodioxole-2-carboxylic acid amide

HRID 745808Notes

Reaction equation

HRID 745808 reaction equation
C([O:3][C:4]([CH:6]1[O:10][C:9]2[CH:11]=[C:12]([CH3:24])[C:13]([S:15]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)(=[O:17])=[O:16])=[CH:14][C:8]=2[O:7]1)=O)C.[NH3:25]>O1CCOCC1>[C:18]1([S:15]([C:13]2[C:12]([CH3:24])=[CH:11][C:9]3[O:10][CH:6]([C:4]([NH2:25])=[O:3])[O:7][C:8]=3[CH:14]=2)(=[O:17])=[O:16])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 539637605-Methyl-6-phenylsulphonyl-1,3-benzodioxole-2-carboxylic acid ethyl ester

Product 1

HCID 543307335-Phenylsulphonyl-6-methyl-1,3-benzodioxole-2-carboxylic acid amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

34.8 g (0.1 mol) of 5-phenylsulphonyl-6-methyl-1,3-benzodioxole-2-carboxylic acid ethyl ester (from Example 2) are dissolved in 350 ml of dioxan (absolute) and treated in a pressure autoclave with approximately 20 g of ammonia gas. The reaction mixture is heated for 10 hours at 80° in the autoclave, the pressure is released, and the solution is concentrated to dryness by evaporation under reduced pressure. The residue is recrystallised from 120 ml of ethanol, yielding colourless crystals of 5-phenylsulphonyl-6-methyl-1,3-benzodioxole-2-carboxylic acid amide having a melting point of 138°-141°.

Workup

  1. temperatureThe reaction mixture is heated for 10 hours at 80° in the autoclave
  2. concentrationthe solution is concentrated to dryness by evaporation under reduced pressure
  3. customThe residue is recrystallised from 120 ml of ethanol

Sources & evidence

ORD record
ord-034e0728bad14461940e12d8a25db720
Source dataset
uspto-grants-1986_07
Patent number
US04600709

Reaction notes

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